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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
25–30 Aug
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4.98 out of 5 average rating, 227 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds
17–22 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Madison
Madison Bay Club House
3 bedrooms, 7 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds
5–10 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds
7–12 Sept
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds
19–24 Aug
5.0 out of 5 average rating, 249 reviews
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds
23–28 Aug
4.94 out of 5 average rating, 189 reviews
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Cambridge
The Sailor’s Shanty
2 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
3 bedrooms, 5 beds
17–22 Aug
5.0 out of 5 average rating, 43 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds
23–28 Aug
4.99 out of 5 average rating, 222 reviews
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5 bedrooms, 10 beds
22–29 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed
22–27 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest house in Cambridge
The Loft at Sailor's Retreat. Waterfront Apartment
1 bedroom, 1 king bed
7–12 Sept
4.99 out of 5 average rating, 117 reviews
Top guest favourite
Home in Fishing Creek
Chesapeake Bay Retreat
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Cambridge
Drop Anchor on the Chesapeake
3 bedrooms, 5 beds
17–22 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds
16–21 Aug
4.97 out of 5 average rating, 157 reviews